Health insurance for IT consultants & tech freelancers

Ryan Michalek, Licensed Health & Life Insurance Agent · NPN 21043091 · Last updated September 15, 2026

Not long ago I helped someone who had just bought out the IT-and-cybersecurity startup he'd been working for. Overnight the group plan that came with that job was gone — and now, consulting and taking on freelance cybersecurity work, he needed real coverage for his whole family, on his own. What mattered to him was a private plan that worked for a business he was still building, and that his CPA could treat as a write-off for the new practice. We found the fit; I pointed the tax side to his accountant to handle. If you've made a jump like that, you're not starting from zero on the coverage question — there's a clear path, and I'll walk it with you.

Why "1099 in tech" changes the coverage question

Independent tech work is 1099 work, and that one fact changes everything about coverage. There's no company plan behind you anymore, no HR portal, no employer quietly paying half the premium. What you get instead is a plan you own outright — on the individual market, in your name, not tied to any single client or contract. That can feel like a downgrade the first time you look at it. It isn't. It means your coverage doesn't end the day a contract does, and it travels with you from one engagement to the next. The mechanics here are the same as they are for any self-employed person; the self-employed health insurance guide is the full walkthrough of options, subsidies, and the tax deduction. This page is about the parts that are specifically a tech consultant's story.

The subsidy cliff most tech consultants hit

Here's the wrinkle that catches a lot of people leaving software, IT, or cybersecurity roles: the work pays well. A strong year consulting or taking on freelance security work can push your household income past the point where a marketplace subsidy applies at all. That's not a reason for discouragement, and it isn't a rate claim — it's just a fork in the road that quietly decides what actually fits. Below that line, a subsidized marketplace plan is often the center of the conversation. Above it, a private under-65 plan is frequently worth pricing side by side, because you're paying the full freight either way and the real question becomes which plan gives you the most for it. Knowing which side of that line you're on is the first thing worth sorting out — and it's exactly the kind of thing a quick, honest call settles.

Covering your family, not just you

For most people making this jump, it was never only about them — there's a spouse, maybe kids, who were on that group plan too. You can absolutely cover your whole household on an individual or private under-65 plan, the same way an employer plan would have. Which route fits leans on two things: your income (see the subsidy question above) and how your family actually uses care — the prescriptions you fill, the doctors you'd rather not give up, anything ongoing. A plan built around how your household really lives is the one that still feels right a year in, instead of the one you resent the first time something important turns out not to be covered.

The write-off — and where your CPA comes in

One of the quieter advantages of going independent: self-employed people can often deduct qualifying health-insurance premiums for themselves and their family. It's an above-the-line deduction, and it comes with rules — it interacts with any months you were eligible for other coverage, and it depends on how your business is structured. That part is genuinely your CPA's department, and it should be; nothing here is tax advice, and I route the specifics to your accountant every time. My job is to get the coverage itself right so there's something worth deducting in the first place. The self-employed guide breaks the deduction down in more detail.

Coverage that keeps up with contract work

Contract work comes in waves — a packed quarter, then a quieter stretch while the next engagement lines up. A plan you own is built for exactly that. It doesn't lapse when a contract ends, it doesn't care which client signs the next statement of work, and it carries straight through the slow months instead of leaving you exposed the moment you can least afford a surprise. The instinct to cancel during a quiet stretch to save the premium is the one thing worth resisting — individual coverage isn't a subscription you pause and restart at will, and a gap is far more expensive than the premium that would have avoided it. If money's genuinely tight between contracts, there are better levers than going uninsured, and walking through those is part of what I'm here for.

Ready to see your options?

If you've left a tech job or gone independent and you're not sure whether you're overpaying — or even covered the right way — start with the coverage cost estimator to see the landscape, then book a quick consultation when you want a real person to walk your specific situation with you. No pressure, no cost to talk.